Revenue Diaries Entry 33

It’s been a busy week, but the positive? I’ve been home for a whole week, which has given me time with the family and more time to write this wonderful newsletter. Here’s what we have today: 

• Remembering D-Day (81 years ago)

• Why marketing might be the hardest job in software

• The AI Maturity Gap (hint: it’s a leadership problem)

• The 80/20 rule that’s shaped my career

Enjoy! 

♥️kyle

On Remembering D-Day

We should talk about it more.

Because everything we love, the life we get to live—none of it was inevitable.

This weekend marks the 81st anniversary of D-Day.

81 years ago, over 150,000 Allied troops landed on the beaches of Normandy. Thousands were killed that day. Thousands more in the days that followed.

I’ve been to those beaches.

And you can’t fully appreciate the magnitude of what happened there until you see it for yourself. The scale. The sacrifice. The sheer chaos of that day.

Honestly, it’s hard to comprehend.

6,000 landing craft. 11,000 planes. 50 miles of coastline. All in the middle of the most destructive war in human history.

And the stakes couldn’t have been higher. The invasion helped turn the tide of World War II and ultimately changed the world.

It’s easy to take that for granted now. I know I do.

The life I get to live, raising my kids, doing work I love, speaking my mind, traveling freely, none of it was guaranteed. It exists because others fought for it. Many made the ultimate sacrifice so that we could have these choices today.

That’s worth remembering. And it’s worth teaching the generations to come.

They should know this story.

On Marketing Being the Hardest Job in Software 

I’ve been thinking about this recently, off the back of another week of meetings. 

One hour, I was talking about the sales pipeline. Next, a brand campaign. Then the product roadmap. Then analyst briefings. Then budget reviews. Then customer marketing.

By the time I got to my last meeting, my brain felt like it had been through a blender.

And it’s pretty obvious but still worth calling out: this is what makes marketing the hardest job in software.

It’s not that marketing is more complex than other functions. It’s not more technical. It’s not even more creative. It’s the sheer amount of context switching the job requires.

If you’re in Sales, your world revolves around pipeline and revenue.

If you’re in Product, you’re building and shipping.

If you’re in Engineering, you’re solving technical problems and scaling systems.

If you’re in Customer Success, you’re driving adoption and retention.

Each of those jobs is hard in it’s own right, no question! But marketing? You have to be in every room. With every stakeholder. Juggling multiple priorities at once.

A typical week looks something like this:

• Meeting with Sales to align on pipeline targets and programs.

• Meeting with Product to prep for a launch.

• Meeting with the CEO to review brand strategy.

• Meeting with Finance to defend next quarter’s budget.

• Meeting with Creative to review campaign concepts.

• Meeting with Analysts to shape industry narrative.

• Meeting with Partners to plan joint marketing.

• Meeting with Customer Success to support renewals and advocacy.

• Meeting with new hires and internal teams to reinforce company culture.

And that’s just the meetings.

In between, you’re writing, editing, building, measuring, presenting — often switching from creative to analytical work in the span of an hour.

You’re expected to be a storyteller, analyst, operator, designer, revenue partner, and spokesperson. Sometimes all in the same day.

That’s what makes this job feel uniquely hard. It’s not any one task — it’s the constant shift between very different types of work, for very different audiences.

And if I’m honest, I haven’t always been great at managing it. I’ve had weeks where I’ve been completely fried by Thursday afternoon.

So I’ve been trying to get a little smarter about it.

Here’s what’s helping me right now:

Protect blocks of deep work:  If I don’t block calendar time, the day will fill itself with meetings. I try to carve out time for deeper, more focused thinking — and I hold that time sacred.

Delegate aggressively: You can’t be in every room or manage every thread. Building a team you trust, and empowering them fully, is the only way to stay sane.

Over-prepare for high-stakes meetings: When switching contexts fast, prep matters. I use a simple checklist or doc to remind myself what matters most in each key meeting.

Build mental reset habits: Even two minutes between meetings — stepping away from my desk, getting some air, reviewing notes — helps clear the slate.

Align leadership on priorities: It’s easy to feel pulled in ten directions. Clear alignment with the CEO, CRO, and CPO on what matters most helps guide where I spend time and energy.

I’m not sure if marketing will always feel this hard. Maybe some of this gets easier with more experience or even using the “robots.” But probably not. 

But I do know this: context switching is part of the job. It’s not a bug. It’s a feature. And the best marketing leaders I know aren’t just great at strategy or creative. They’ve learned how to move between worlds. 

On the AI Maturity Gap

A few days ago, I saw this image from Zapier making the rounds. A simple chart, showing how different teams can move from Unacceptable → Capable → Adaptive → Transformative in their use of AI.

You can review the content, because it’s good, but the c

The gap from Capable to Transformative is where most companies are living right now. And it’s damn wider than most people and leaders would care to admit. 

Here’s what I see:

• Teams can draft copy with ChatGPT.

• They can summarize call notes or build a basic automation.

• They’ve tested AI copilots in their tools.

But very few teams have integrated AI into how they operate, compete, or grow. They’ve adopted AI. But it hasn’t transformed their work.

Why?

It’s not a tooling problem. The tools are here. Anyone can spin up a Claude or GPT-4o instance in 30 seconds.

It is a skills problem.
Getting to “adaptive” and “transformative” use of AI requires new skills:

• Knowing what to automate and what not to.

• Building AI-driven workflows that integrate into daily work.

• Prompting well enough to move beyond generic outputs.

• Designing processes that combine human expertise with AI speed.

• Rethinking how your function creates value because of AI.

Most people haven’t been taught these skills. And most leaders haven’t created the space or expectation to learn them.

It’s also a leadership problem.  Most leaders haven’t reset expectations. They haven’t told their teams: "This is not optional anymore."

Here’s what I’m telling my teams right now:

1. You’re expected to be at least “Adaptive.”  If you’re still manually handling tickets, writing copy from scratch, or dismissing AI as “hype,” you’re behind. Full stop.

2. We will create the time to invest. The companies moving fast on AI aren’t doing it because they magically have more hours in the week. They make time. They ship 90% work to save 50% time. They block time to experiment. We need to do the same.

3. This is about competitiveness, not efficiency. Yes, AI will help us save time. But that’s the wrong lens. The right lens is:

   1. Can we create more relevant and personalized content at scale?

   2. Can we shorten cycles from idea to campaign to market?

   3. Can we elevate the customer experience across every touchpoint?

   4. Can we use AI to better understand buying behavior and drive smarter decisions?

Those are competitive advantages. That’s why this matters.

Every leader I know is talking about AI adoption. Very few are leading it. If you’re not setting a clear expectation and helping your team close the gap, you can’t expect them to move beyond “Capable.”

The companies that do? They’ll win.

On the 80/20 Rule That’s Guided My Career

Last week, I was on a call with someone in the learning tech space, smart, seasoned operator. Toward the end of the conversation, they asked:

"How do you know when it’s time to leave a job?"

It’s one of my favorite questions. Because every career looks neat and linear in hindsight. But when you’re in it, when you’re sitting in that seat, deciding whether to stay or go is anything but clear.

Here’s the simple rule that’s guided me: 80% of the job should energize you. 20% can be crap.

That’s a healthy ratio. Every role has hard days, annoying meetings, messy politics, or stuff you simply don’t want to do.

But when that 20% starts creeping toward 50% or higher?  When half your time is spent frustrated, disengaged, or questioning whether it’s worth it?

That’s the signal. It’s time to step back and ask why.

For me, that moment usually comes when I lose the connection to the work.

Sometimes it happens slowly. You take on a role because it stretches you…  a new market, a new stage, a new skill set. That’s good. That’s growth. But over time, if you can’t connect to what you’re building or the problem you’re solving, it starts to show. You’re not as effective. You don’t bring the same energy. And the job starts to feel heavier than it should.

When that happens, I pay attention. It’s usually a sign it’s time for a new challenge.

The other thing I shared on that call: every job change should feel like a pivot, not just more of the same. If you’re going to jump, do it for growth. Pick a role that forces you to level up… new industry, new stage, new skillset, or new kind of leadership challenge.

Don’t just swap the same problems for a different logo.

If you’re in a season where the 20% feels heavier than it should, pay attention to that feeling. It’s worth listening to.